Boomers Wait Too Long, Millennials Don’t Wait Long Enough

We weren't made to pay bills, save for our glorified 10-year retirement, and die.

We also weren’t made to live for the present, aka YOLO, and never plan for tomorrow.

Being purely hedonistic, as millennials have a very strong tendency to be, results in a life devoid of long-term wins and hard-earned purpose. I learned this while pursuing unfettered happiness as opposed to some form of happiness derived from satisfaction. Satisfaction typically happens after some duration of suffering that leads to happiness in the suffering being finished.

Boomers are obviously hedonistic as well; all Americans are, but boomers have a much higher likelihood of having long-term discipline due to a stronger propensity to be religious, committed to raising their children, and their long-duration oriented 401ks. The boomers as kids were the partying hippies, while their parents, the silent generation, fought two world wars. Millennials as kids were the student debt-fueled, digital flexers while their parents, the boomers, flexed IRL with the white picket fence and big house. Every subsequent generation becomes less ascetic and more hedonist. A shorter attention span = a shorter duration of enduring self-discipline, and a lackluster ability to play the long game.

Easy life, hard choices. Hard life, easy choices.

Proof of life for Kelsey

Millennials could take a page from the boomers’ playbook and be loyal to their profession while saving for a rainy day decades later. The issue with this is millennials saw their boomer parents go through the self-discipline of saving for their retirements before being around to see the fruits of their labors in their golden years. As kids, we grew up hearing the exhortations of boomers to “never do what they did.” I heard this more times than I could count while playing adult beer league hockey in my teens. Perhaps it's also just wanting to not do what your parents did as a form of rebellion - either way, the result is the same. Live for today - tomorrow is tomorrow’s problem. Book the trip to Tulum, Eat, Pray, Love, YOLO.

Choose your suck.

There are always actionable truths in generalities and broad sweeping statements that allow us to avoid the plight of the commons. Boomers, by and large, buy into the system, put in their decades at their 9-5s, and save. The generation before them, the silent generation, was even more ascetic. The partying boomers in their younger years looked even crazier than millennials or zoomers do to boomers nowadays. Of course, I’m speaking in generalities, so please allow me the space to say the obvious, which is there are always exceptions to the rules. One such exception is the Pardeys.

Lin & Larry Pardey, both of the staunchly traditionalist silent generation, set sail on Larry’s 31st birthday after having stocked away all their savings from mostly selling nylon rope in years prior under a boat services company they built in California . Their business was really starting to pick up right around the time they completed Seraffyn, their Lyle Hess-designed 24’ channel cutter. By some accounts, they were stumbling on solving the same problem that Randy Repass, the founder of West Marine, was solving with his business around the late 60s - the same time in which The Pardeys were operating. The timing was there, and the Pardey’s had the knowledge to scale the company into something massive to compete with West Marine. We all know how this story ends with The Pardey’s completing 2 engineless circumnavigations, living a life of consummate adventure. There is something to be said about their consciously deciding not to scale their business and sticking to the plan of sailing their newly built boat as far as it’ll take them, “as long as it’s fun.”

Build your own boat - then go small, go simple, and go now.

As Dr. Andrew Huberman would say, grow your anterior midcingulate cortex by doing hard things. There is so much beauty on the other side of discipline and struggle. The key is not to let it lose its sting, or else you’re not actually growing anymore. That’s when you embody the boomer mind and just stock away your 40+ years for a promising golden decade. Routine is undeniably powerful - we just can’t let routine become routine. As David Goggins says in the podcast link at the start of this paragraph, there is no carrot - it’s just the dangon stick.

Abandon Comfort.

For the past 5 years, 90% of the time, Kelsey and I have lived with no running water or heat all up and down the East Coast. Southern Appalachia to Northern Appalachia to the heart of the city, calling full-gut construction zones home. All while we are making 5x more money than we did while working our corporate 9-5s, living in far worse conditions than we did back then. Our income has risen substantially while our living expenses have gone down as low as they possibly can. This is all temporary, voluntary, and in pursuit of our shared dream. Our current life is some weird masochist combination of Goggins-lite suffering, Into the Wild extremist freedom, and Pursuit of Happyness monetary drive. Perhaps we might miss out on our own version of scaling into a West Marine level business but no offense to Randy Repass, the Pardey’s stories are a lot more interesting to us.

More on that next post once we’re back to a more sunny, southern place…